Propyne → (r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(5-methyl-isoxazol-3-yl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

HRID 545581ノート

反応式

HRID 545581 の反応式
[CH:1]#[C:2][CH3:3].[F:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[CH2:8][N:9]1[C:21]2[CH2:20][CH2:19][C@@H:18]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([CH:28]=[N:29][OH:30])[CH:14]=2>C(Cl)Cl.[O-]Cl.[Na+]>[F:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[CH2:8][N:9]1[C:21]2[CH2:20][CH2:19][C@@H:18]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([C:28]1[CH:1]=[C:2]([CH3:3])[O:30][N:29]=1)[CH:14]=2

参加物

5

反応物 2

HCID 6335PropyneHCID 87305657(r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

生成物 1

HCID 59161297(r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(5-methyl-isoxazol-3-yl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 23665760Sodium Hypochlorite溶媒

反応条件

温度
23 °C

実験手順

Bubble propyne gas through a solution of (R)-cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amide (Example 203) (0.065 g, 0.16 mmol) in methylene chloride and NaOCl solution maintained in a sealed tube. Cap the tube and stir at 23° C. for 16 h. Partition the reaction between methylene chloride and water. Separate and dry the organic portion over Na2SO4 to give 0.045 g of a tan solid. Purify by silca gel chromatography, eluting with 20-80% EtOAc/gradient to give an 0.030g (42%) of an off-white solid. mp: 190-192° C.; MS (ES): m/z 444 (M+1).

後処理

  1. temperaturemaintained in a sealed tube
  2. customCap the tube
  3. customPartition
  4. customthe reaction between methylene chloride and water
  5. customSeparate
  6. dry with materialdry the organic portion over Na2SO4

出典と根拠

ORDレコード
ord-e242ecea617240a88b1166e9f019eb15
出典データセット
uspto-grants-2011_05
特許番号
US07935722B2

反応ノート

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